0.28 mi
Distance
| Address | Bed / Bath | Listing Price |
|---|---|---|
30 Prospect St
One of Winchester’s most beloved neighborhoods sets the tone for 30 Prospect Street, a beautifully reimagined home transformed by an extensive remodel less than five years ago. A spectacular, fully renovated Chef's kitchen anchors the main level with high-end finishes and a seamless flow for livin
Living Area:
2519 Sqft.
|
4
Beds,
3
Baths
|
$2,099,000 |
89 Wildwood St
Welcome to 89 Wildwood — Winchester’s best new value, where modern design meets classic New England charm! This new construction home offers a flexible layout with spaces for hosting, relaxing & everyday living. The chef’s kitchen impresses with an oversized island, stylish finishes, ample cab
Living Area:
4929 Sqft.
|
7
Beds,
6
Baths
|
$2,299,000 |
139 High Street
This charming Cape style home on a half-acre lot combines classic character with modern updates. Step inside to find newly refinished hardwood floors throughout the inviting fireplaced living room, dining room, and bedrooms. The recently updated kitchen and bathrooms blend style and function with co
Living Area:
1302 Sqft.
|
3
Beds,
2
Baths
|
$999,000 |
9 Norfolk Rd
This beautifully updated Winchester residence combines timeless Garrison-style architecture with elegant modern finishes, creating a seamless space for everyday living. The inviting foyer leads to a sunlit living room, where wide-plank oak flooring flows into a stunning chef’s kitchen equipped wit
Living Area:
4320 Sqft.
|
6
Beds,
4
Baths
|
$2,399,000 |
8 Felsdale Close
Nestled in one of Winchester's most picturesque cul-de-sacs, this elegant English Tudor is available for the first time in 60 years. Passed quietly through word of mouth, this is a rare opportunity to own a piece of Winchester's architectural history. Located near Lincoln School & Winchester Fells'
Living Area:
3658 Sqft.
|
4
Beds,
3
Baths
|
$2,075,000 |
6 Marchant Road
Updated 3 bed, 2.5 bath home *Set on a generous 11K lot* in a fantastic Winchester location/ Lincoln Elementary close to town, schools, the train, and route to Boston. The first floor offers an ideal layout with an updated kitchen, stainless steel appliances & island w seating open to a lovely famil
Living Area:
2153 Sqft.
|
3
Beds,
3
Baths
|
$1,350,000 |
237 Swanton Street
NEWER CONSTRUCTION! This 2020 home showcases 5 beds, 4 baths-4300sf of style & luxury situated on the corner of Loring Ave. The home features high ceilings, hardwood floors & a stunning sunny open floor plan w/ eat in kitchen, center island, custom cabinetry, stainless appliances & walk-in pantry. F
Living Area:
4334 Sqft.
|
5
Beds,
4
Baths
|
$2,149,000 |
12 Canterbury Road
Tucked along a quiet side street in the sought-after Ambrose School district, this spacious ranch offers comfort, convenience, and endless possibilities. With nearly 2,000 square feet of living space, the home features seven rooms, including a large living room w/ fireplace that anchors the easy, na
Living Area:
1942 Sqft.
|
3
Beds,
3
Baths
|
$1,200,000 |
446 Highland Ave
Charming Spanish-style home in desirable Winchester! This unique property features a beautiful terracotta roof and timeless architectural details. The first floor welcomes you with a foyer which leads to an astounding great room, perfect for entertaining or hosting family gatherings. The kitchen ope
Living Area:
2033 Sqft.
|
2
Beds,
2
Baths
|
$999,000 |
209 Washington St
Charm and character meet modern living in this beautifully renovated & expanded Victorian townhome just steps from Winchester Center. Fully updated in 2013/14 with new kitchen, baths, wiring, all systems, roof, and windows—and enhanced in 2023 with a redesigned patio, landscaping, fencing, and flo
Living Area:
3141 Sqft.
|
5
Beds,
4
Baths
|
$1,499,000 |
5 Wood Lane
Royal Barry Wills former home! – An architectural treasure nestled on over 1 acre of land in one of Winchester’s most serene and private settings. Designed by the renowned architect Royal Barry Wills, this iconic Cape Cod residence showcases timeless elegance with its signature gambrel roof, cy
Living Area:
2443 Sqft.
|
3
Beds,
3
Baths
|
$1,950,000 |
8 Priscilla Ln
Welcome to 8 Priscilla Ln, Winchester—a brand-new 5 bed, 5.5 bath luxury home designed by Salt & Stone Co where elevated craftsmanship meets everyday comfort. Spanning 6,500 ± sq ft, this home features a chef’s kitchen with custom cabinetry, premium appliances, and an oversized center island fl
Living Area:
6500 Sqft.
|
5
Beds,
6
Baths
|
$3,250,000 |
53 Winford Way
Stunning new construction in highly sought-after Winchester! This thoughtfully designed home blends modern style with everyday functionality. The first floor features an open-concept kitchen, dining area, and sun-filled living and family rooms with soaring ceilings open to the second floor and a coz
Living Area:
5083 Sqft.
|
5
Beds,
4
Baths
|
$2,799,000 |
15 Wildwood Street
Welcome to 15 Wildwood Street — a quintessential Winchester residence offering timeless character, modern amenities & endless potential. Ideally situated on a beautiful lot close to the town center. This charming home is impeccably maintained & move-in ready, while providing the opportunity for th
Living Area:
4104 Sqft.
|
6
Beds,
3
Baths
|
$2,275,000 |
53 Bacon Street
Location, Location, Location! This beautifully maintained 3-bedroom, 2.5 bath multi-level home perfectly balances convenience and suburban charm. Enjoy an easy walk to the commuter rail, downtown shops and restaurants, schools, parks, and more. The main level features a spacious, sun-filled open flo
Living Area:
2865 Sqft.
|
3
Beds,
3
Baths
|
$1,499,000 |
40 Foxcroft Road
An extremely rare new construction in the Flats, this stunning 6BD/4.5BA home is a ground-up rebuild blending modern luxury with timeless warmth in one of Winchester’s most coveted neighborhoods. Designed for elevated living, it features a chef’s kitchen with quartz counters, custom cabinetry, a
Living Area:
6367 Sqft.
|
6
Beds,
5
Baths
|
$3,799,000 |
80 Arlington St
New roof. New landscaping. New exterior paint. New price! With its coveted setting, elegant bones, and enduring charm, this Royal Barry Wills home awaits your personal design statement. Ideally located on the 4th green of Winchester Country Club’s storied Donald Ross-designed course, this beloved
Living Area:
5632 Sqft.
|
5
Beds,
4
Baths
|
$3,099,000 |
44 Cabot Street
Welcome to 44 Cabot Street, a newly built home in one of Winchester’s most desirable neighborhoods. Offering over 6,000 square feet of beautifully crafted space, this residence features 6 bedrooms, 6.5 bathrooms, and a layout designed for modern living. Thoughtfully selected finishes, high ceiling
Living Area:
6028 Sqft.
|
6
Beds,
7
Baths
|
$3,099,000 |
380 Cross St
This Expanded Cape features a fireplace living room, built in bookcases, and glistening hardwood floors throughout. The spacious kitchen has a dining area which opens to the living room for an entertaining atmosphere. The 2nd floor Master bedroom suite has a balcony to enjoy your morning coffee. The
Living Area:
1938 Sqft.
|
4
Beds,
2
Baths
|
$949,000 |
2 Everett Ave
Welcome to one of Winchester’s most extraordinary residences. This one-of-a-kind Center Entrance Colonial Revival sits on a beautifully landscaped, private lot complete with in-ground swimming pool and ample outdoor space perfect for relaxation or entertaining. A grand foyer welcomes you in where
Living Area:
7043 Sqft.
|
7
Beds,
6
Baths
|
$4,174,000 |
20 Grove Pl
From the moment you enter this European-style Victorian, you’ll be charmed. The first level features an eat-in kitchen with quartz countertops, LG Café appliances, wine fridge, island, and large windows, plus a living room, den, and half bath. The second floor offers a primary suite with skylight
Living Area:
3294 Sqft.
|
5
Beds,
4
Baths
|
$1,869,000 |
4 Chestnut St
Space to grow, room to gather, and a location that feels like home. Just blocks from Winchester’s town center, commuter rail, and nearby schools, this warm and distinctive home offers four levels of flexible living. A vaulted-ceiling living room sets the tone, while the custom kitchen features blu
Living Area:
4474 Sqft.
|
4
Beds,
5
Baths
|
$1,990,000 |
7-9 Cleveland Rd
Welcome to this outstanding home set on a spacious 20,817 sf lot in desirable Winchester. This property presents a wealth of possibilities, whether you're looking to live in it as a single-family home, have a need for an in-law apartment, or maintain it as a multi-family residence. The 1st level boa
Living Area:
2578 Sqft.
|
5
Beds,
3
Baths
|
$1,149,000 |